Benzaldehyde → 5-PHENYLDIPYRROMETHANE

HRID 1794645Notes

Reaction equation

HRID 1794645 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH:6](=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(O)(C(F)(F)F)=O>[CH:10]1[CH:11]=[CH:12][C:7]([CH:6]([C:2]2[NH:1][CH:5]=[CH:4][CH:3]=2)[C:5]2[NH:1][CH:2]=[CH:3][CH:4]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 240Benzaldehyde2×HCID 8027Pyrrole2×

Product 1

HCID 43275135-PHENYLDIPYRROMETHANE

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Gas Chromatography. We previously reported that the GC trace of the crude reaction mixture, obtained with TFA catalysis, shows three major peaks.16 The GC trace of the crude reaction mixture obtained with 0.1 equiv of InCl3 and a pyrrole:benzaldehyde ratio of 100:1 for 1 h also shows three major peaks (FIG. 2A) that are assigned as 1 (tR=16.4 min), 2 (tR=17.0 min) and 3 (tR=21.8 min) based on comparison with authentic samples. Closer scrutiny of the same GC trace upon amplification of the scale reveals a number of additional minor peaks (FIG. 2B). The appearance and intensity of these minor peaks depend on the reaction conditions (catalyst, reaction time, and pyrrole:benzaldehyde ratio). For example, some of the minor peaks seen in InCl3 catalyzed reactions are not observed in TFA catalyzed reactions.

Sources & evidence

ORD record
ord-bbd5890e03544b1e8e1a5851e25dc430
Source dataset
uspto-grants-2006_04
Patent number
US07022862B2

Reaction notes

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